This trailhead is at the Ventana Canyon Resort. Your first job is to drive to the resort, which can be done in any number of ways. One way is to drive to Grant (or Kolb) and Tanque Verde, then take Tanque Verde to Sabino Canyon Road and thence north. Sabino Canyon Road will split off to the right, but you keep going straight, the roads name now changes to Kolb and leads you right to the resort. (Don't enter a gated community at a road labelled "Ventana Canyon Drive", but go two roads beyond this, there is a sign for the trailhead. Another way is to go north on Craycroft forever. Craycroft will turn to the east, then turn to the south, change names to Kolb, and take you to the trailhead road described above.
At the resort, take the first left from the entrance drive and follow the signs to the trailhead parking on the west side of the resort, behind the employee parking lot. On my visit in 2010, there were plenty of signs to clearly lead you to the parking area.
Ventana, by the way, is spanish for "window".
The trailhead is at 3000 feet elevation. The first mile or so of the trail is via an "access corridor" next to apartments and such. Hiking up the trail 2.4 miles brings you to "Maiden Pools" (approx 4200 elevation), (a good destination for a short hike). I have never been overwhelmed by the pools at this location, but this spot is just past the culmination of a strenuous bit of climbing. Another 2.8 miles (5.2 total) brings you to a trail junction at 6000 feet elevation. The left branch goes another 2.3 miles (for 7.5 total) to the top of Mount Kimball (7255 feet). The right branch goes 1.2 miles to Window Peak (6.4 miles total, 7468 feet elevation).
There are numerous possibilities from the head of Ventana Canyon. You could procede on to Cathedral Peak (another 4 miles from Window peak for 10.4 miles total one way). You could hike down Esperero Canyon, Finger Rock Canyon, or even Pima Canyon.
I hiked most of the above March 11, 2010. At that time there was snow on the upper part of the trail (from around the Kimball junction and above). The stream was a rushing torrent that needed to be carefully crossed at many spots. The view of Cathedral Peak was of snow and ice and ice encrusted trees. I turned around on the ridge below "the window" at 6600 foot elevation, and so did about a 12 mile loop (and 3600 foot climb) in 8 hours and was thoroughly thrashed.
This area is claimed to be part of the "Desert Bighorn Sheep Wilderness area" (is there such a thing) and some restrictions apply. The aim of these rules is good, namely giving the bighorn sheep a chance to survive. In particular, no dogs; and no off-trail hiking or camping from January 1 through April 20. (No doubt, all this is subject to change year by year and moment to moment). The information on the Forest Service website for this trail is ridiculously out of date, particularly the trailhead information. You can try calling the Coronado National Forest website at 520-388-8300 to ask about the bighorn sheep lambing season closure.
I don't know (but am curious) what the guidelines are for overnight parking at this trailhead.
Tom's hiking pages / tom@mmto.org